Sulfanilamide → Methyl 2-{[(4-aminobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoate

HRID 897007Notes

Reaction equation

HRID 897007 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([NH:23][C:24](OC2C=CC=CC=2)=[O:25])[C:16](=[CH:21][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:24]([NH:23][C:15]2[CH:14]=[C:13]([Cl:12])[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])=[O:25])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5333SulfanilamideHCID 15524163HCID 15524163, compound

Product 1

HCID 22347486Methyl 2-{[(4-aminobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoateYield 131.1%

Procedure

From 2.7 g (15.7 mmol) of 4-aminobenzenesulfonamide and 4.8 g (15.7 mmol) of methyl 4-chloro-2-N-phenoxycarbonylanthranilate in a manner similar to Preparation Example 1, 7.9 g (yield 94%) of methyl 2-{[(4-aminobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoate was obtained. Property: colorless amorphous, PMR (δppm, DMSO-d6): 3.59 (3H, s), 5.37 (2H, s), 6.45 (2H, d), 6.83 (1H, dd), 7.41 (2H, d), 7.81 (1H, d), 8.66 (1H, d), 9.64 (1H, s).

Sources & evidence

ORD record
ord-f5f0d7a92356441eb5b63e22004b05bc
Source dataset
uspto-grants-2005_07
Patent number
US06921766B1

Reaction notes

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